First anal

I was maybe 21, I'd been working the summer in a hotel, nights, so I always finished breakfast time, and used to go to a café on the beach where a surfer guy started going. Eventually I caught his eye, and over the next few days we went from kissing, to sucking and eventually to fucking - me fucking him, he never asked to fuck me - this was also 30+ years ago before we thought about HIV, STDs etc. We were making out, he sucked me and got me really wet, turned round, laying on his front told me to lay on top of him he took my sloppy wet dick, put it to his ass and told me to push into him, it felt quite rough on my uncut head, and after taking a break when he told me to get lots of spit around his hole, eventually I pushed in and felt him opening up, he felt very tight but then it was like a pop and I was through and I remember him saying wow push slower, which I did. he told me to push all the way in which I did, then he started rising his ass back into me and grinding onto my dick. I came pretty quick that first time, but I stayed in him and stayed hard and we finally got into a bit of a rhythm. Next time I saw him I knew a bit better what I needed to do, and it was a bit better. all the same just felt so natural with him. Still remember him and those days fondly:)
 
First time was going to happen but never did. Was with a guy with a huge cock and we were wrestling around and he put his arms around my stomach and pulled me close to him, his cock jabbed me dead center of my hole! I saw stars! It never happen that night or with him sadly, wanted to know the feeling of a huge cock! Finally happen with someone else and I thought I got this and eagerly sat on top of his cock and proceeded to jam it all in, it hurt And had to take it slow!
 
my first anal was with a caring and wonderful older man. i was 19 at the time and he took me home with him, gave me a cocktail, a jazz cigarette and slowly undressed me. He took me into the bedroom and told me everything he wanted me to do as well as what he was going to do. I was his after the weekend and he showed me the splendours of gay sex to which i am always thankful.
 
what was your first time having anal sex like? When did you try it and why?
When I was 13 with a 14 year old friend who was already hung I like it much I let fuck every day for six months unfortunately he moved away and we lost touch it was before Broadband and cheap mobile phones
 
When I was 13 with a 14 year old friend who was already hung I like it much I let fuck every day for six months unfortunately he moved away and we lost touch it was before Broadband and cheap mobile phones

Mate, firstly don't talk about sexual experiences before you reached the age of 18. It violates the ToS on the site.

Secondly, calm down the posting. You're averaging one post per minute in this sub-forum right now